Tetrahedron Letters

Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines

MY Chang, CH Lin, TW Lee

Index: Chang, Meng-Yang; Lin, Chung-Han; Lee, Tein-Wei Tetrahedron Letters, 2012 , vol. 53, # 6 p. 627 - 631

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Citation Number: 3

Abstract

A simple three-step synthetic routes toward 2-substituted 3-diarylmethylenylpiperidines 7 (Y= CN) and 8 (Y= allyl) starting with 3-diarylmethylenylpiperidines 9 is described. The process was carried out by the bromomethoxylation of skeleton 9 with NBS in MeOH at reflux for 2h, regioselective α-dehydrobromination with DBU in THF at reflux for 10h, and BF3· OEt2-catalyzed cross-coupling of the corresponding enamine with trimethylsilyl- ...